Multicomponent synthesis of novel thiazolo[3,2-a]pyridin-8-yl-phosphonates as a model of plant growth regulator

Abstract

A series of thiazolo[3,2-a]pyridin-8-yl-phosphonate derivatives have been obtained by the reaction of diethyl (E)-((4-oxothiazolidin-2-ylidene)methyl)phospohonate, malononitrile and two equivalent of various aromatic aldehydes in a multicomponent reaction with good yields. The structures of the new compounds are confirmed by spectroscopic methods (IR, 1H, 13C, 31P NMR and HRMS). Compound diethyl-(Z)-(5-amino-6-cyano-2-(4-nitrobenzylidene)-7-(4-nitrophenyl)-3-oxo-3,7-dihydro-2H-thiazolo[3,2-a]pyridin -8-yl)phosphonate (4k) at 1 mM concentration enhanced biomass plant height, number of branches and leaf area of tomato plants of at least two-fold compared to the control plants. In common bean plants, this compound enhanced the chlorophyl content and delayed senescence in comparison to the control plants. Therefore, in future studies, the compound(s) would be further tested to evaluate deeply their mode of action at physiological, biochemical and molecular level to finally enhance crop productivity of various plants.